This invention relates to curable adhesive compositions for dental use.
A number of adhesive compositions have been proposed for orthodontic and restorative treatments. Typical are catalyzed compositions comprising a radical polymerizable monomer such as an acrylate or methacrylate vinyl monomer. For example, Japanese Patent Application Kokai No. 60-44508 proposes a curable composition comprising an acrylate or methacrylate vinyl monomer, an aromatic carboxylic acid or anhydride containing an acryloyloxyl or methacryloyloxyl group, an amine, and a sulfinic acid or a salt thereof. Japanese Patent Application Kokai No. 53-39331 discloses an adhesive composition comprising an acrylate or methacrylate ester which is liquid at room temperature, an amine, a sulfinic acid or a salt thereof, and a peroxide. Nihon Shika Hoken (Japanese Dental and Hygienic Journal), 28, 270 (1985) reports an adhesive composition comprising methyl methacrylate, 4-META, and a partial oxide of tributylboran (TBB-O). However, most conventional adhesives and curable compositions fail to sufficiently bond and fit to tooth substance, particularly, dentin treated with a mild etching agent such as ethylenediaminetetraacetic acid (EDTA) and non-etched dentin.